


Sex Education – Winchester Style – Dr. Dean

by Wayward_and_Worn



Series: Sex Education - Supernatural Style [1]
Category: Supernatural
Genre: Multi, Oral Sex, Poly Relationship, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2018-12-21
Updated: 2018-12-21
Packaged: 2019-09-23 20:57:33
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,270
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17087621
Author URL: https://archiveofourown.org/users/Wayward_and_Worn/pseuds/Wayward_and_Worn
Summary: Dean happens to discover that Y/N is having orgasm issues.  She gets close and then it just fizzles out.  She’s pretty frustrated and has agreed to let Dean and Sam “school her” in the art of pleasure.





	Sex Education – Winchester Style – Dr. Dean

**Author's Note:**

> I try not to think too hard about HOW Dean found out. But I'm sure it was funny. 
> 
> Forgive my raging tense issues. It's plagued me my whole life.

“Are you ready for the lesson?”  Dean smiled down at Y/N, who was lying on her bed in just an oversized shirt stolen from Sam. 

She nodded, “teach me, oh knowledgeable one.”  She smirked. 

“Very funny.”  Dean scoffed, removing his flannel and draping it over the headboard of her bed like he always did.  “You see,” he began as he kicked off his boots and stepped up onto her bed, “the orgasm isn’t simply an orgasm.”  He kicked the pillows onto the floor and stood just behind her.  He nudged her forward a little, wedging himself between her and the headboard.  His hands came around and rested on her bare thighs.  Her skin tingled at the contact.  “It’s a delicious, burning, all-encompassing release of desire that has risen and risen until it could no longer be contained.”  He ran his hands up her sides, under the shirt, pulling it over her head and tossing it to the floor. She shivered but not with cold.

The feel of his fully clothed body behind her felt erotic and strange. “And if you’re just trying to get off for getting offs sake,” she felt him shrug, “this is what happens sometimes.” She felt his lips at the nape of her neck. “And that’s just tragic.”

Just then, they heard footsteps outside her door. They stopped, and a solid knock echoed through her room.  “Come in.” She was surprised that her voice sounded strained.

Sam entered dressed only in sweatpants. His hair was still damp from his shower.  He studied his brother and their lover.  “Am I late, Professor?”  He smirked as he closed the door behind him.

                “It’s Doctor, Bitch, and no you’re not late.  Now shut up and listen.  Y/N here is unintentionally giving herself ruined orgasms.”  The elder Winchester replied. “I know for some people, that’s a thing. But I really don’t think it’s her thing.”  She shook her head.

“That’s terrible.” Sam answered. Coming to stand next to the bed where Dean’s hands had been running over her skin. He leaned down to kiss her. “Why not let us make you come?  You know we can.”  He let one hand cup her breast, squeezing gently.  “You know we like to.”

She sighed against his soft lips. “You’ve been so busy with everything...I didn’t want to bother you with something so trivial.”  Sam snorted and looked up at Dean. 

The brothers had a silent conversation over her head and her body tingled with anticipation.  She turned to try to see Dean’s face as his hand came up to cup her other breast.  Kneading gently just like his brother.  She moaned softly as Dean’s fingers gently pulled at her now taut nipple.  

“We’re gonna give you an orgasm so good, they’re gonna hear you topside.” Dean’s voice was low at her ear.  She shivered again.  “Let’s continue the lesson.”

Without words, Sam moved to the easy chair against the wall at the foot of the bed.  He plopped down, his legs relaxed, knees apart. From there he could see everything.  Her legs spread out before him, he felt his erection growing.

“How about you start, Sammy?”

Nodding, Sam began palming himself through the sweats. His eyes fastened on the two in the bed.  Heat pulsed in her core at the sight.

“See,” Dean’s breath was a soft caress over her naked shoulder. “Sam was already turned on before he knocked.  He was turned on just by the thought of you.  And now by looking at you.  Naked and,” his large hands gripped her thighs, pushing them farther apart, “Open.”  She pushed back into Dean’s chest. Her body responding to Dean’s hands and Sam’s hungry gaze.  She whimpered while Dean hummed in response.  “And me?” He pushed his hips against her back and she could feel his hardness even through his jeans. “Of course, I’m turned on.  You always turn me on.”

Y/N brought her arms up and around to grasp his biceps and her head fell back against his shoulder.  He kissed her neck again, then nipped at it.

“Focus, sweetheart. We’re learning today.”

She raised her head and focused again on Sam.  “Bend your knees,” he commanded.  She obliged, pulling her legs up and bracing her heels on the bed, she let her legs fall open wider. “Yes.”

“Good girl.” Dean praised with another kiss to her neck.  “Some people, especially you, respond well to commands.  It adds to the wanting.  Stokes the fire, so to speak.”  Resting his chin on her shoulder, he addressed his brother, “You turned on Sammy?”

“Yes.”

“How do you know?”

“I’m hard,” he grunted as he grasped himself tightly and tugged.  “So very hard.”  She felt another rush as Sam let his head fall back on the back of the chair with a soft moan.   

His lips returned to her ear, “How about you Y/N?  Are you turned on?”

She nodded, unable to form words.

“How do you know?” He ran his hands along the inside of her thighs.

She squirmed a little, wanting to press her thighs together.  “Because I’m-- “ she gasped as Dean’s fingers dipped inside her.

“Wet.”  He finished.

“Yes.”  Her voice breathy and soft.  

“But it’s not good enough to just be wet. You need to be dripping.  You need to be hungry.”  He looked up, “Sam, come make her wetter. “

A wolf's grin appeared on the younger Winchester’s face as he fluidly rose from the chair and ambled to the bed. “With pleasure.”  When his knees hit the bed, he let himself fall forward, landing on his fists just in front of her.  Turning his head, he kissed the inside of her right knee. Then kissed farther down, continuing until she felt his breath ghost over her exposed core. Then he shifted to the base of her left leg and kissed his way up to her left knee.

Her fingers dug into Dean’s arm as she whined in protest. “It’s about the buildup too darlin’, not just the end.” He whispered as he watched his brother tease her.  “And I believe you will be screaming.” 

Sam dragged his tongue down her inner thigh, stopping to bite the soft flesh just hard enough to leave marks.  She yelped, and she felt a new rush of wetness.  She squirmed more in Dean’s grasp and he tightened his hands on her.  “Safe word if you need it.  Otherwise...Be.  Good.”  Dean growled.

She couldn’t help her wanton moan and her head falling back against his shoulder.  This time she wasn’t scolded, but the moment her eyes were off Sam, he slipped his tongue against her clit.  She hollered and arched away from Dean as pleasure shot to the tips of her fingers and down to her curled toes.  

“Open her more.”  Sam said thickly.

Dean wrapped one arm under each of her knees, pulling her legs up and back, tilting her hips up towards Sam and pulling her open wide.  She felt her thighs burning with the stretch and moaned Dean’s name. 

“I love that sound.”  He purred.  “Better Sam?”

Sam didn’t answer, instead, he let out a low growl and spread her pussy lips with his fingers, immediately diving in again with his tongue.  

“Sam!”  She cried.  She tried to move her hips against him, but Dean held her still.  

“Feel that?  You want so bad for more.  That burn in the center of your body, throbbing, needing that one special touch.  But you’re not getting it.  Not now.  So it burns.  It burns, and it grows.”  Dean’s breath was becoming labored.  His hardened cock like a shotgun barrel against her back.  “And that’s what you want.  You want that need, that desperate craving for that one touch.  That way, you will have no choice but to come.  Completely.”  He sucked a mark onto the back of her shoulder.  “Sam.” 

Sam gave one final swipe of his tongue and slid back.  Dean released her legs and they fell to the bed.  She was gasping.  He was right, her whole body was screaming for more.  She watched as Sam stood at the foot of her bed, slid his thumbs into the waist of his sweats and pushed them to the floor.  He stepped out of them and took his throbbing cock back into his hand.  Stroking as he stared hard at her.  

“How do you feel now, Sam?”  Dean asked as casually as if he were talking about the weather.  

Sam’s hazel eyes were burning with an intense desire she’d only seen a couple of times.  Without moving his attention from her, he answered, “I need her.”

Dean dragged his tongue from the nape of her neck to the sensitive spot behind her ear.  “And you?”

She felt like she was vibrating.  “I want him.”  She arched her back, pulled her legs back up, and moaned, “I want you Sam.  I need you.”

“You feel that burning?” Dean asked.  One of his hands sliding down her stomach to her soaked core.

“Yes.”

“Do you like it?”  He pressed a finger against her swollen clit, rubbing in circles so gently she was about to scream.

Her eyes fluttered closed.  “Yes.  More.  Harder.”  She gasped, her hands gripping his arms tighter.  “Please.”

“Look at Sam.”

She opened her eyes to see Sam, still standing at the end of the bed, panting, sliding his dick through his hand.  The room fell silent.  Dean continuing to tease her clit while her eyes roamed over Sam.     

After an eternity stretched out between them. “Let’s make her cum.”  Dean said. 

 

“Finally.”  Sam blurted, crawling back onto the bed.  He slotted himself between her legs, grabbing her thighs and pulling her up so that she was draped over his lap.  He immediately notched  himself at her entrance.  Dean adjusted his position so that he could still hold her but not have her bent in half.  Dean’s fingers increasing the pressure and speed as Sam sheathed himself in her.  He began pumping his hips in a slow, strong rhythm.  Already grunting with pleasure, she felt his cock tighten as it slid through her folds.    

“Sam...Dean…” she gulped in shock, “I’m already… I’m gonna…”

“Cum for us.”  Sam growled. 

“Cum now.”  Dean whispered as he increased his pressure on her clit just a bit more.  

She screamed.  She screamed long and loud.  She screamed their names.  She screamed obscenities.  She was bucking and writhing in Dean’s arms as Sam grabbed her legs to keep himself buried inside her.  As she was rocked by orgasmic spasms, she was also aware of a roar of release from Sam as he pulsed inside her.

Dean’s hands slipped away and dropped to his thighs.  Without him holding her, she almost melted into the mattress. She felt boneless, weightless, and satisfied. Sam was back in the chair, looking like she felt. A sated smile of his own gracing that handsome face.   

Once she caught her breath, she tipped her head back to look up at the handsome hunter.  “How do you feel, Dean?”  He turned his emerald eyes to hers and she could easily see in his blown pupils how turned on he was.  She could also see traces of sweat gathered at his hairline.

He licked his lips.  “I’m hard.”  He finally replied, palming himself with a slight grunt.  “I’m so hard that it hurts.”

“Do you want me?”

“Yes,” He then dipped his head down, capturing her mouth in a needy kiss. His hands moved to cup and squeeze her breasts.  “Now I need you.”  He breathed before claiming her lips again.  His tongue greedy and firm.  She couldn’t help but move into his hands.  Reluctantly breaking the kiss, she pulled herself up onto her hands and knees and turned to face him.

A gasp behind her from Sam reignited her desire.  She pushed her knees apart to give him a better view.  She rocked forward again to meet Dean’s mouth.  This time his hand fisted in her hair, while his other worked at opening his belt. She balanced on her knees and reached down to assist.  Soon his weeping cock was free and being caressed by Y/N’s hands.  He grunted with each tug; his hand, still in her hair, pulled her back to his mouth.

“Do _you_ want to cum?” She asked.

“Yes.”

She sat back on her heels, allowing Dean to bring his own legs together.  As she crawled forward, he wrestled his jeans down to his thighs.  She swung her leg over him and he reached for her. 

“Come here, baby.” his voice was like bourbon as she positioned.  She slid down on his cock, the two of them moaning together.  Holding her tightly, he began thrusting up into her oversensitive cunt.  She wrapped her arms around his shoulders, her chest rubbing against his shirt.  The material causing her nipples to tingle with the friction.  Dean dipped his head down to catch a nipple in his mouth, he bit down gently and she arched with a cry.

“Y/N, I’m--” he began, but he didn’t have a chance to finish.  He came hard with a shout and a gasp of her name as his whole body locked.  She wrapped around him, feeling each twitch of his cock as it released.  He held her in silence for a few minutes until his body relaxed.  

“That was amazing,” she said against his ear.  

“I hope you learned something.”  Dean said, his lips dragging along her throat.   

She nodded.  “Yes.”

“Good,” he rumbled, pulling her head back to meet her eyes.  “Because there will be a test tomorrow.”


End file.
